Secord began his military career in Southeast Asia, flying over 285 combat missions and involvement in the CIA's "secret war" in Laos. Later on, he teamed up with his old friend Albert Hakim and started something called "the Enterprise", which was part business empire (arms deals) and part military and security operations (covert warfare and intelligence). Within two years, "the Enterprise" had five aircraft, two-dozen pilots, a few airfields, and a hoard guns and other military equipment.

Secord and his Enterprise realized their first major financial gain on the sale of missiles to then Ayatollah Khomeini to the tune of $16 Million Dollars, of which he received a $2.2 million dollar share.

In 1988, Secord was indicted for defrauding the U.S. government and implicated in a small controversy called the Iran/Contra Affair.